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Identification
NameAmbenonium
Accession NumberDB01122  (APRD00771)
TypeSmall Molecule
GroupsApproved
DescriptionAmbenonium is a cholinesterase inhibitor used in the management of myasthenia gravis. [Wikipedia]
Structure
Thumb
Synonyms
Ambenonium
Ambenonium base
Ambenonum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MysuranNot Available
MytelaseNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ambenonium chloride
ThumbNot applicableDBSALT001309
Categories
UNIIL16PUN799N
CAS number7648-98-8
WeightAverage: 537.565
Monoisotopic: 536.268482022
Chemical FormulaC28H42Cl2N4O2
InChI KeyOMHBPUNFVFNHJK-UHFFFAOYSA-P
InChI
InChI=1S/C28H40Cl2N4O2/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30/h9-16H,5-8,17-22H2,1-4H3/p+2
IUPAC Name
[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium
SMILES
CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl
Pharmacology
IndicationAmbenonium is used to treat muscle weakness due to muscle disease (myasthenia gravis).
Structured Indications Not Available
PharmacodynamicsAmbenonium, similar to pyridostigmine and neostigmine, is used for the treatment of muscle weakness and fatigue in people with myasthenia gravis. It is postulated to exert its therapeutic effect by enhancing cholinergic function through the inhibition of the acetylcholine hydrolysis by acetylcholinesterase. Increased levels of acetylcholine has peripheral effects, as acetylcholine is also used in the brain, where it tends to cause excitatory actions. The glands that receive impulses from the parasympathetic part of the autonomic nervous system are also stimulated in the same way. This is why an increase in acetylcholine causes a decreased heart rate and increased production of saliva. Ambenonium is used less commonly than neostigmine or pyridostigmine but may be preferred in patients hypersensitive to the bromide ion. Ambenonium produces fewer muscarinic side effects than neostigmine, but more than pyridostigmine.
Mechanism of actionAmbenonium exerts its actions against myasthenia gravis by competitive, reversible inhibition of acetylcholinesterase. The disease myasthenia gravis occurs when the body inappropriately produces antibodies against acetylcholine receptors, and thus inhibits proper acetylcholine signal transmission (when acetylcholine binds to acetylcholine receptors of striated muscle fibers, it stimulates those fibers to contract). Ambenonium reversibly binds acetylcholinesterase at the anionic site, which results in the blockage of the site of acetycholine binding, thereby inhibiting acetylcholine hydrolysis and enhancing cholinergic function through the accumulation of acetycholine at cholinergic synpases. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.
TargetKindPharmacological actionActionsOrganismUniProt ID
AcetylcholinesteraseProteinyes
inhibitor
HumanP22303 details
Related Articles
AbsorptionOral - poorly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Plasma and hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=150±44 mg/kg (orally in mice). Symptoms of overdose include muscle twitching, weakness and paralysis of voluntary muscles including the tongue, shoulders, neck and arms, blood pressure increase (with or without a slowing of heart rate), a sensation of internal trembling, severe anxiety, and panic. Death may occur rapidly if untreated.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Ambenonium.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Ambenonium.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Ambenonium.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Ambenonium.Experimental, Illicit
AcebutololAmbenonium may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Ambenonium.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Ambenonium.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Ambenonium.Experimental
AlprenololAmbenonium may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Ambenonium.Approved
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Ambenonium.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Ambenonium.Approved
Aop200704Ambenonium may increase the bradycardic activities of Aop200704.Investigational
ArecolineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Arecoline.Experimental
ArotinololAmbenonium may increase the bradycardic activities of Arotinolol.Approved
AtenololAmbenonium may increase the bradycardic activities of Atenolol.Approved
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Ambenonium.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Ambenonium.Approved, Vet Approved
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Ambenonium.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Ambenonium.Approved, Investigational
BefunololAmbenonium may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Ambenonium.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Ambenonium.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Ambenonium.Approved, Vet Approved
BetaxololAmbenonium may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Ambenonium is combined with Bethanechol.Approved
BevantololAmbenonium may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Ambenonium.Approved
BisoprololAmbenonium may increase the bradycardic activities of Bisoprolol.Approved
BopindololAmbenonium may increase the bradycardic activities of Bopindolol.Approved
BucindololAmbenonium may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Ambenonium.Approved
BufuralolAmbenonium may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololAmbenonium may increase the bradycardic activities of Bupranolol.Approved
CarbacholThe risk or severity of adverse effects can be increased when Ambenonium is combined with Carbachol.Approved
CarteololAmbenonium may increase the bradycardic activities of Carteolol.Approved
CarvedilolAmbenonium may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololAmbenonium may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Ambenonium.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Ambenonium.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Ambenonium.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Ambenonium.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Ambenonium.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Ambenonium.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Ambenonium.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Ambenonium.Approved, Investigational
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Ambenonium.Investigational
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Ambenonium.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Ambenonium.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Ambenonium.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Ambenonium.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Ambenonium.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Ambenonium.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Ambenonium.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Ambenonium.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Ambenonium.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Ambenonium.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Ambenonium.Approved
DipyridamoleThe therapeutic efficacy of Ambenonium can be decreased when used in combination with Dipyridamole.Approved
EPIBATIDINEThe risk or severity of adverse effects can be increased when Ambenonium is combined with EPIBATIDINE.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Ambenonium.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Ambenonium.Approved
EsmololAmbenonium may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Ambenonium.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Ambenonium.Approved
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Ambenonium.Approved
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Ambenonium.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Ambenonium.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Ambenonium.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Ambenonium.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Ambenonium.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Ambenonium.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Ambenonium.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Ambenonium.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Ambenonium.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Ambenonium.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Ambenonium.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Ambenonium.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Ambenonium.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Ambenonium.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Ambenonium.Approved, Investigational, Withdrawn
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Ambenonium.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Ambenonium.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Ambenonium is combined with GTS-21.Investigational
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Ambenonium.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Ambenonium.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Ambenonium.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Ambenonium.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Ambenonium.Approved
IndenololAmbenonium may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Ambenonium.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Ambenonium.Investigational
LabetalolAmbenonium may increase the bradycardic activities of Labetalol.Approved
LevobunololAmbenonium may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Lobeline.Investigational
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Ambenonium.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Ambenonium.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Ambenonium.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Ambenonium.Vet Approved
MethacholineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Ambenonium.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Ambenonium.Approved, Vet Approved
MetipranololAmbenonium may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Ambenonium.Approved
MetoprololAmbenonium may increase the bradycardic activities of Metoprolol.Approved, Investigational
MivacuriumAmbenonium may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Ambenonium.Approved, Vet Approved
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Ambenonium.Vet Approved
NadololAmbenonium may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Ambenonium.Investigational
NicotineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Nicotine.Approved
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Ambenonium is combined with Nicotine bitartrate.Approved
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Ambenonium.Investigational
Oleoyl estroneThe risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Ambenonium.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Ambenonium.Approved
OxprenololAmbenonium may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Ambenonium.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Ambenonium.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Ambenonium.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Ambenonium.Approved
PenbutololAmbenonium may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Ambenonium.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Pilocarpine.Approved
PindololAmbenonium may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Ambenonium.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Ambenonium.Approved
PractololAmbenonium may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Ambenonium.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Ambenonium.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Ambenonium.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Ambenonium.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Ambenonium.Experimental
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Ambenonium.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Ambenonium.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Ambenonium.Investigational
PropranololAmbenonium may increase the bradycardic activities of Propranolol.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Ambenonium.Approved
RapacuroniumAmbenonium may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Ambenonium.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Ambenonium.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Ambenonium.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Ambenonium.Approved
SotalolAmbenonium may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Ambenonium.Approved
TimololAmbenonium may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Ambenonium.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Ambenonium.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Ambenonium.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Ambenonium.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Ambenonium.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ambenonium.Approved
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Ambenonium.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Ambenonium.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Ambenonium.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Ambenonium.Approved
VareniclineThe risk or severity of adverse effects can be increased when Ambenonium is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Ambenonium.Approved
Food InteractionsNot Available
References
Synthesis Reference

Kirchner, F.K.; U.S. Patent 3,096,373; July 2,1963; assigned to Sterling Drug Inc.

General ReferencesNot Available
External Links
ATC CodesN07AA30
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (166 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9618
Blood Brain Barrier+0.8373
Caco-2 permeable+0.5168
P-glycoprotein substrateSubstrate0.8725
P-glycoprotein inhibitor INon-inhibitor0.6717
P-glycoprotein inhibitor IINon-inhibitor0.766
Renal organic cation transporterNon-inhibitor0.823
CYP450 2C9 substrateNon-substrate0.7865
CYP450 2D6 substrateNon-substrate0.7008
CYP450 3A4 substrateSubstrate0.5842
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.6899
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.538
Ames testNon AMES toxic0.7312
CarcinogenicityNon-carcinogens0.6118
BiodegradationNot ready biodegradable0.9927
Rat acute toxicity2.4379 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9665
hERG inhibition (predictor II)Inhibitor0.8507
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Mytelase 10 mg caplet1.86USD caplet
Mytelase 10 mg tablet1.86USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point196-199 °CKirchner, F.K.; U.S. Patent 3,096,373; July 2,1963; assigned to Sterling Drug Inc.
water solubilitySolubleNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.42e-07 mg/mLALOGPS
logP2.27ALOGPS
logP-3.6ChemAxon
logS-8.8ALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity173.57 m3·mol-1ChemAxon
Polarizability59.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Quaternary ammonium salt
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Lockhart B, Closier M, Howard K, Steward C, Lestage P: Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. Naunyn Schmiedebergs Arch Pharmacol. 2001 Apr;363(4):429-38. [PubMed:11330337 ]
  2. Hodge AS, Humphrey DR, Rosenberry TL: Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities. Mol Pharmacol. 1992 May;41(5):937-42. [PubMed:1588924 ]
  3. Papp MI, Komoly S, Szirmai IG, Kovacs T: Similarities between CSF-brain extracellular transfer and neurofibrillary tangle invasion in Alzheimer's disease. Neurobiol Aging. 2006 Mar;27(3):402-12. Epub 2005 Jun 27. [PubMed:15982786 ]
  4. Kenakin TP, Beek D: Self-cancellation of drug properties as a mode of organ selectivity: the antimuscarinic effects of ambenonium. J Pharmacol Exp Ther. 1985 Mar;232(3):732-40. [PubMed:2857786 ]
  5. Webb GD: Affinity of benzoquinonium and ambenonium derivatives for the acetylcholine receptor, tested on the electroplax, and for acetylcholinesterase in solution. Biochim Biophys Acta. 1965 May 25;102(1):172-84. [PubMed:5833399 ]
  6. Bolognesi ML, Cavalli A, Andrisano V, Bartolini M, Banzi R, Antonello A, Rosini M, Melchiorre C: Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors. Farmaco. 2003 Sep;58(9):917-28. [PubMed:13679187 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Yamamoto K, Kohda Y, Sawada Y, Iga T: Pharmacokinetics of ambenonium, a reversible cholinesterase inhibitor, in rats. Biopharm Drug Dispos. 1991 Nov;12(8):613-25. [PubMed:1801966 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23